Literature DB >> 27293370

Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Cyclic Electrophiles.

Samantha E Shockley1, Jeffrey C Holder1, Brian M Stoltz1.   

Abstract

This account describes our laboratory's efforts in the development of a palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic conjugate acceptors. Specifically, we highlight the study of this transformation in the following areas: (a) construction of all-carbon quaternary stereocenters, (b) elucidation of the reaction mechanism, (c) addition to heterocyclic acceptors to generate tertiary stereocenters, and (d) application in the synthesis of natural products.

Entities:  

Keywords:  asymmetric; catalysis; conjugate addition; palladium

Year:  2015        PMID： 27293370      PMCID： PMC4896742          DOI： 10.1021/acs.oprd.5b00169

Source DB:  PubMed          Journal:  Org Process Res Dev        ISSN： 1083-6160            Impact factor:   3.317


  48 in total

1.  Regiodivergent 1,4 versus 1,6 asymmetric copper-catalyzed conjugate addition.

Authors:  Hélène Hénon; Marc Mauduit; Alexandre Alexakis
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers.

Authors:  David Martin; Stefan Kehrli; Magali d'Augustin; Hervé Clavier; Marc Mauduit; Alexandre Alexakis
Journal:  J Am Chem Soc       Date:  2006-07-05       Impact factor: 15.419

3.  Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: a highly enantioselective pathway for accessing chiral flavanones.

Authors:  Qijie He; Chau Ming So; Zhaoxiang Bian; Tamio Hayashi; Jun Wang
Journal:  Chem Asian J       Date:  2015-01-13

4.  Formation of quaternary chiral centers by N-heterocyclic carbene-Cu-catalyzed asymmetric conjugate addition reactions with Grignard reagents on trisubstituted cyclic enones.

Authors:  Stefan Kehrli; David Martin; Diane Rix; Marc Mauduit; Alexandre Alexakis
Journal:  Chemistry       Date:  2010-08-23       Impact factor: 5.236

5.  Pd(II)-bipyridine catalyzed conjugate addition of arylboronic acid to alpha,beta-unsaturated carbonyl compounds.

Authors:  Xiyan Lu; Shaohui Lin
Journal:  J Org Chem       Date:  2005-11-11       Impact factor: 4.354

6.  Meldrum's acids and 5-alkylidene Meldrum's acids in catalytic carbon-carbon bond-forming processes.

Authors:  Aaron M Dumas; Eric Fillion
Journal:  Acc Chem Res       Date:  2010-03-16       Impact factor: 22.384

7.  Copper-catalyzed asymmetric conjugate addition with chiral SimplePhos ligands.

Authors:  Laëtitia Palais; Alexandre Alexakis
Journal:  Chemistry       Date:  2009-10-12       Impact factor: 5.236

8.  Readily available [2.2.2]-bicyclooctadienes as new chiral ligands for Ir(I): catalytic, kinetic resolution of allyl carbonates.

Authors:  Christian Fischer; Christian Defieber; Takeyuki Suzuki; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2004-02-18       Impact factor: 15.419

9.  Copper-catalyzed asymmetric conjugate addition of trialkylaluminium reagents to trisubstituted enones: construction of chiral quaternary centers.

Authors:  Magali Vuagnoux-d'Augustin; Alexandre Alexakis
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

10.  Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones.

Authors:  Cornelia L Boeser; Jeffrey C Holder; Buck L H Taylor; K N Houk; Brian M Stoltz; Richard N Zare
Journal:  Chem Sci       Date:  2015-03       Impact factor: 9.825
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  8 in total

1.  Enabling the Cross-Coupling of Tertiary Organoboron Nucleophiles through Radical-Mediated Alkyl Transfer.

Authors:  David N Primer; Gary A Molander
Journal:  J Am Chem Soc       Date:  2017-07-18       Impact factor: 15.419

2.  Stereoselectivity Predictions for the Pd-Catalyzed 1,4-Conjugate Addition Using Quantum-Guided Molecular Mechanics.

Authors:  Jessica Wahlers; Michael Maloney; Farbod Salahi; Anthony R Rosales; Paul Helquist; Per-Ola Norrby; Olaf Wiest
Journal:  J Org Chem       Date:  2021-03-26       Impact factor: 4.354

Review 3.  Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development.

Authors:  Jennifer K Matsui; Simon B Lang; Drew R Heitz; Gary A Molander
Journal:  ACS Catal       Date:  2017-03-14       Impact factor: 13.084

4.  Direct α-Arylation/Heteroarylation of 2-Trifluoroboratochromanones via Photoredox/Nickel Dual Catalysis.

Authors:  Jennifer K Matsui; Gary A Molander
Journal:  Org Lett       Date:  2017-01-12       Impact factor: 6.005

5.  Formation of quaternary centres by copper catalysed asymmetric conjugate addition to β-substituted cyclopentenones with the aid of a quantitative structure-selectivity relationship.

Authors:  Ruchuta Ardkhean; Mike Mortimore; Robert S Paton; Stephen P Fletcher
Journal:  Chem Sci       Date:  2018-02-05       Impact factor: 9.825

Review 6.  Recent advances in palladium-catalysed asymmetric 1,4-additions of arylboronic acids to conjugated enones and chromones.

Authors:  Jan Bartáček; Jan Svoboda; Martin Kocúrik; Jaroslav Pochobradský; Alexander Čegan; Miloš Sedlák; Jiří Váňa
Journal:  Beilstein J Org Chem       Date:  2021-05-10       Impact factor: 2.883

7.  Formal Giese addition of C(sp3)-H nucleophiles enabled by visible light mediated Ni catalysis of triplet enone diradicals.

Authors:  Geun Seok Lee; Soon Hyeok Hong
Journal:  Chem Sci       Date:  2018-06-11       Impact factor: 9.825

Review 8.  Leveraging Fleeting Strained Intermediates to Access Complex Scaffolds.

Authors:  Sarah M Anthony; Laura G Wonilowicz; Matthew S McVeigh; Neil K Garg
Journal:  JACS Au       Date:  2021-06-23
  8 in total

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